Cowboy Boots: What to Wear (and Not to Wear) With Them

Welcome, all you fashion-savvy cowgirls and cowboys! 

Are you ready to embrace your inner Wild West spirit while staying true to your stylish sensibilities?

If so, you’ve moseyed into the right place.

In this blog post, we’re going to rustle up some fabulous outfit ideas that’ll have you kicking up your heels in delight.

From the dusty trails of the countryside to the bustling sidewalks of the city, cowboy boots have blazed their way into the hearts and closets of fashionistas everywhere. 

But how do you style these versatile and iconic kicks without looking like you just stepped off a ranch?

Fear not, partner! We’ve got your back. 

We’ll be exploring tops, jeans, shorts, skirts and dresses that pair flawlessly with cowboy boots, ensuring you look chic and stylish while paying homage to this classic American footwear.

So saddle up, grab your hat, and let’s dive into a world of denim, floral prints, and leather as we help you create unforgettable ensembles that’ll have you saying, “Yeehaw!” in no time. 

Let the fashion rodeo begin!

Here’s what to wear with cowboy boots.

Dresses That Pair Flawlessly with Cowboy Boots

Cowboy boots and dresses may not seem like the most obvious pairing, but when done right, they can create a stunning and unique look. 

This combination is perfect for those who want to add a touch of rustic charm to their feminine wardrobe. 

In this section of our blog post, we’ll explore various dress styles that pair exceptionally well with cowboy boots, helping you create unforgettable outfits for any occasion.

Midi Dresses: 

A midi dress that hits just below the knee is an excellent choice for pairing with cowboy boots. 

The length is perfect for showcasing your boots without overwhelming your outfit. 

Opt for a flowy or A-line silhouette for a breezy, effortless look.

Maxi Dresses: 

Maxi dresses are a great option for a more bohemian vibe when paired with cowboy boots.

The long, flowing fabric contrasts beautifully with the rugged charm of the boots. 

Choose a dress with side slits or a high-low hem to reveal a glimpse of your boots as you walk.

Denim Dresses: 

A denim dress is a natural choice for wearing with cowboy boots, as it complements the boots’ Western roots. 

From shirt dresses to fit-and-flare styles, there’s a denim dress for every taste. 

Pair with a statement belt to accentuate your waist and complete the look.

Floral Dresses: 

Embrace your feminine side by pairing a floral dress with your cowboy boots. 

The combination of delicate blooms and rugged boots creates a charming and unexpected contrast. 

Opt for smaller prints and lighter colors to keep the focus on your boots.

Shirt Dresses: 

Shirt dresses offer a casual and comfortable option for wearing with cowboy boots. 

The button-down design and collared neckline provide structure and balance to the look.

 Choose a dress in a solid color or a subtle pattern to let your boots take center stage.


For a fun, flirty outfit, try wearing a sundress with your cowboy boots. 

The combination of a lightweight, breezy dress and sturdy boots is perfect for warm-weather events or casual outings. 

Look for dresses with ruffles, lace, or other feminine details to enhance the contrast between the dress and the boots.

Sweater Dresses: 

When the temperatures drop, don’t hesitate to pair your cowboy boots with a cozy sweater dress. 

This combination is both stylish and practical, keeping you warm and comfortable while still looking chic. 

Opt for a more fitted dress to balance the bulkiness of the boots.

Little Black Dress: 

Believe it or not, the classic little black dress can also work well with cowboy boots. 

The key is to choose a more casual LBD with a simpler design, allowing the boots to shine. 

Pair with statement accessories to create a striking and sophisticated look.

Remember, when pairing dresses with cowboy boots, it’s essential to balance the feminine and rugged elements of your outfit. 

Don’t be afraid to experiment with different dress styles and accessories to find the perfect combination that showcases your personality and style.

Finding the Perfect Jeans to Rock with Your Cowboy Boots

This is a super obvious answer to what to wear with cowboy boots.

Denim and cowboy boots are a match made in fashion heaven. 

This combination is versatile, comfortable, and always on-trend. 

However, finding the perfect pair of jeans to wear with your cowboy boots can be a challenge. 

In this section of our blog post, we’ll discuss various styles of jeans and denim that pair exceptionally well with cowboy boots, ensuring you look fabulous every time you step out in this iconic duo.

Bootcut Jeans: 

As the name suggests, bootcut jeans are specifically designed to accommodate boots, making them an excellent choice for your cowboy boots. 

The slight flare at the bottom of the jeans allows the boots to be showcased while providing a balanced, flattering silhouette.

Straight-Leg Jeans: 

Straight-leg jeans offer a classic, timeless look that pairs wonderfully with cowboy boots. 

This style of denim is versatile and works well for both casual and dressier occasions. For a more polished look, opt for a darker wash.

Skinny Jeans: 

Skinny jeans are another popular choice for wearing with cowboy boots. 

To pull off this look, tuck your jeans into your boots to create a sleek, streamlined appearance. Choose a stretchy denim material for added comfort and ease of movement.

Distressed Denim: 

If you’re going for a more rugged, lived-in vibe, distressed jeans are the way to go. 

The worn-in look of distressed denim adds character and texture to your outfit, perfectly complementing the rustic charm of cowboy boots.

High-Waisted Jeans: 

High-waisted jeans are not only flattering but also incredibly stylish when paired with cowboy boots. 

The higher waistline elongates your legs and creates an elegant silhouette. 

Tuck in your top or wear a crop top to accentuate your waist even more.

Cropped Jeans: 

For a modern twist on the classic denim-and-cowboy-boots combo, try wearing cropped jeans. 

This style exposes a bit of your boots, drawing attention to their unique details. 

Opt for a raw or frayed hem for added visual interest.

Wide-Leg Jeans:

If you’re feeling adventurous, consider pairing your cowboy boots with wide-leg jeans. 

This combination creates a bold, fashion-forward look that’s sure to turn heads. 

To balance the proportions, wear a more fitted top and tuck it into your jeans.

When it comes to choosing the perfect jeans to wear with your cowboy boots, consider factors like fit, style, and wash. 

Remember, the key is to find a combination that showcases your personal style and flatters your figure. 

Don’t be afraid to experiment with different styles and embrace the unique flair that cowboy boots bring to any outfit.

Styling Cowboy Boots with Skirts and Shorts

Embracing the cowboy boot trend doesn’t mean you have to forego your favorite skirts and shorts. 

With the right combination, you can create chic, playful, and even sophisticated looks that perfectly showcase your beloved boots.

In this section, we’ll discuss various skirt and short styles that complement cowboy boots, ensuring you look and feel fabulous all year long.

Denim Skirts: 

A denim skirt is a natural choice when it comes to styling cowboy boots. 

The quintessential Western fabric, denim pairs effortlessly with cowboy boots for a cohesive and stylish look. 

Opt for mini, midi, or maxi lengths, depending on your personal preference and the occasion.

Midi Skirts: 

Midi skirts that hit just below the knee are a fantastic option for pairing with cowboy boots.

The length allows your boots to shine while providing a flattering and balanced silhouette.

Choose skirts with a flowy or A-line cut to create a breezy, feminine look.

Maxi Skirts:

 For a bohemian twist, try wearing a maxi skirt with your cowboy boots. 

The combination of a long, flowing skirt and rugged boots creates an eye-catching contrast. 

Opt for skirts with slits or a high-low hem to show off your boots as you walk.

Pencil Skirts: 

For a more polished and sophisticated ensemble, consider pairing your cowboy boots with a pencil skirt. 

This unexpected combination is perfect for making a statement at the office or a night out. 

Choose a skirt in a neutral color or subtle pattern to keep the focus on your boots.

Mini Skirts: 

Embrace your playful side by wearing a mini skirt with cowboy boots. 

This fun and flirty combination is perfect for casual outings, concerts, or festivals. 

Pair with tights or knee-high socks during colder months for added warmth and style.

High-Waisted Shorts: 

High-waisted shorts are not only trendy but also incredibly flattering when worn with cowboy boots. 

The higher waistline elongates your legs and creates a balanced, chic look. 

Opt for denim, linen, or tailored shorts to suit your personal style.

Denim Shorts: 

Denim shorts are a versatile and popular choice for styling with cowboy boots. 

Their casual, laid-back vibe perfectly complements the rugged charm of the boots, creating a balanced and fashionable look. 

Opt for different washes, distressed detailing, or frayed hems to add variety to your ensemble. 

For a more polished appearance, choose a pair of cuffed denim shorts and pair them with a stylish belt to accentuate your waist. 

This combination is ideal for warm-weather outings, concerts, or casual weekend adventures.

When styling cowboy boots with skirts and shorts, don’t be afraid to mix and match different fabrics, lengths, and patterns to create unique and fashionable looks. 

The key is to find a combination that highlights your personal style and allows your cowboy boots to shine. 

Experiment with various styles and accessories to create unforgettable outfits that make you feel confident and stylish.

Styling Your Cowboy Boots: Perfect Tops to Complete Your Look

If you’re struggling to find the perfect top to complement your cowboy boots, worry not! 

We’ve got you covered.

Let’sl discuss various tops that go exceptionally well with cowboy boots, no matter the occasion or style you’re aiming for.

Denim Shirts: 

You can never go wrong with a classic denim shirt when it comes to pairing with cowboy boots. 

This timeless combination exudes a casual yet chic vibe. 

Opt for lighter or darker shades of denim to create a stylish contrast with your boots.

Plaid Button-Downs: 

A plaid button-down shirt is an ideal choice for a laid-back country look. 

Choose bold colors or more subtle hues, depending on your personal style and the color of your cowboy boots.

Roll up the sleeves for a more casual vibe or tuck it into your jeans to accentuate your waist.

Flowy Blouses: 

For a more feminine touch, consider pairing your cowboy boots with a flowy blouse. 

This combination is perfect for creating a boho-chic look that is both comfortable and stylish. 

Opt for blouses with floral prints, lace detailing, or off-the-shoulder designs to make a statement.

Graphic Tees:

For a more casual and edgy look, try pairing your cowboy boots with a graphic tee. 

This combination allows you to express your personality while still rocking those fabulous boots. 

Tuck your tee into a pair of high-waisted jeans or let it hang loose for a relaxed vibe.

Peplum Tops: 

If you’re looking for a more sophisticated outfit, try wearing a peplum top with your cowboy boots. 

The fitted waist and flared hem of a peplum top can create a flattering silhouette that pairs beautifully with the rugged charm of cowboy boots.

Sweaters and Cardigans: 

For chillier days or evenings, don’t be afraid to pair your cowboy boots with a cozy sweater or cardigan. 

Opt for oversized knits or fitted turtlenecks to create a stylish ensemble that keeps you warm and comfortable.

Crop Tops: 

For a more daring and trendy look, try pairing your cowboy boots with a crop top. 

This combination is perfect for making a statement at concerts or festivals. 

Complete the look with high-waisted jeans or a maxi skirt for added drama.

When it comes to styling cowboy boots, the possibilities are endless. 

The key is to choose a top that reflects your personal style while also complementing the boots. 

Experiment with different combinations, and don’t be afraid to step out of your comfort zone.

Avoiding Fashion Faux Pas: What NOT to Wear with Cowboy Boots

So now you know what to wear with cowboy boots.

But what about what not to wear with them?

Cowboy boots are a versatile and stylish addition to any wardrobe. 

However, there are certain fashion choices that can clash with the Western aesthetic or create an unflattering look when paired with cowboy boots. 

In this section of our blog post, we’ll discuss items you should avoid wearing with cowboy boots to ensure that you always look chic and put-together.

Overly Formal Attire: 

Cowboy boots are inherently casual, making them a poor choice for pairing with overly formal attire such as ball gowns or tuxedos. 

The combination can look mismatched and awkward. Instead, opt for dressier shoes that complement the formality of the event.

Athleisure Wear: 

While cowboy boots are versatile, they don’t mix well with athletic wear like yoga pants, leggings, or sweatpants. 

The two styles clash, and the result is an uncoordinated and disjointed look. 

Stick to casual, everyday outfits or more bohemian styles when wearing your cowboy boots.

Tight Mini Skirts: 

Although mini skirts can work with cowboy boots, avoid tight, body-hugging mini skirts that don’t provide enough balance for the boots. 

Instead, opt for A-line or flowy mini skirts that create a more harmonious silhouette.

Competing Patterns: 

Cowboy boots often feature intricate embroidery or bold designs. 

To avoid visual clutter, steer clear of clothing with busy patterns or competing designs that could clash with your boots.

Instead, choose solid colors or subtle patterns that allow your boots to take center stage.

Too Many Western Accents: 

While it’s tempting to go all-out with the Western theme, avoid wearing too many Western-inspired pieces together, such as fringed jackets, cowboy hats, and bolo ties. 

This can result in an overly-costumey appearance. 

Instead, balance your cowboy boots with more contemporary or minimalist pieces to create a cohesive and stylish outfit.

Ill-Fitting Jeans: 

When pairing jeans with cowboy boots, it’s essential to choose a well-fitting pair that complements your boots. 

Avoid jeans that are too baggy or too long, as they can make your outfit look unkempt and unflattering. 

Opt for bootcut, straight-leg, or skinny jeans that fit comfortably and showcase your boots to their full potential.

Overly Bold Accessories: 

Cowboy boots are often a statement piece on their own. 

To avoid overpowering your outfit, steer clear of overly bold accessories like large, chunky necklaces, or oversized belts.

Instead, opt for more delicate or understated accessories that complement your boots without overwhelming your look.

Remember, the key to rocking cowboy boots is to balance their unique, Western charm with contemporary and stylish clothing choices. 

By avoiding these fashion faux pas, you’ll be well on your way to creating chic and unforgettable outfits that showcase your cowboy boots in the best possible light. 

I hope you enjoyed my post on what to wear with cowboy boots.

Happy styling!

Our article about going sock less in cowboy boots may help you here!